(2S)-2-[(1S)-2-nitro-1-phenylethyl]-2H-furan-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2S)-2-[(1S)-2-nitro-1-phenylethyl]-2H-furan-5-one
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: ACZKKHWPGKXBLW-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三甲硅氧基-2-呋喃 、 β-硝基苯乙烯 在 S-联萘酚磷酸酯 作用下， 反应 6.0h， 生成 (2S)-2-[(1S)-2-nitro-1-phenylethyl]-2H-furan-5-one 、 5-(2-nitro-1-phenylethyl)furan-2(5H)-one
  参考文献：
  名称：

  布朗斯台德酸催化的硝基烯烃中 2-三甲基甲硅烷氧基呋喃的无溶剂有机催化向山-迈克尔加成反应

  摘要：

  在无溶剂条件下，布朗斯台德酸促进了 2-三甲基甲硅烷氧基呋喃与硝基烯烃的首次有机催化 Mukaiyama-Michael 加成反应。用各种取代的硝基烯烃以中等至良好的产率进行共轭加成。该程序操作简单，无需任何后处理。

  DOI：

  10.1055/s-0029-1217970

文献信息

• Solvent-Free Organocatalytic Mukaiyama-Michael Addition of 2-Trimethylsilyloxy Furan to Nitroalkenes Catalyzed by Brønsted Acids
  作者：Arrigo Scettri、Maria Acocella、Vincenzo De Sio、Rosaria Villano

  DOI：10.1055/s-0029-1217970

  日期：2009.10

  The first organocatalytic Mukaiyama-Michael addition of 2-trimethylsilyloxy furan to nitroalkenes was promoted by Bronsted acids under solvent-free conditions. The conjugate addition took place in moderate to good yields with variously substituted nitroalkenes. The procedure is operationally simple and no workup is required.

  在无溶剂条件下，布朗斯台德酸促进了 2-三甲基甲硅烷氧基呋喃与硝基烯烃的首次有机催化 Mukaiyama-Michael 加成反应。用各种取代的硝基烯烃以中等至良好的产率进行共轭加成。该程序操作简单，无需任何后处理。
• Mukaiyama-Michael vinylogous additions to nitroalkenes under solvent-free conditions
  作者：Arrigo Scettri、Rosaria Villano、Patrizia Manzo、Maria Acocella

  DOI：10.2478/s11532-011-0122-7

  日期：2012.2.1

  dioxinone-derived silyl ether to nitroalkenes is reported. The conjugate addition is performed in absence of any catalyst under solvent-free conditions, proceeding with satisfactory efficiency with variously substituted nitroalkenes.Moreover, the first organocatalyzed Mukaiyama-Michael vinylogous reaction of trimethylsilyloxyfuran to nitroalkenes is described.The reaction is promoted by Brønsted acids under

  报道了二恶英衍生的甲硅烷基醚与硝基烯烃的第一次 Mukaiyama-Michael 乙烯系反应。共轭加成是在无溶剂条件下在没有任何催化剂的情况下进行的，与各种取代的硝基烯烃以令人满意的效率进行。此外，描述了三甲基甲硅烷氧基呋喃到硝基烯烃的第一个有机催化的 Mukaiyama-Michael 乙烯基反应。该反应由布朗斯台德酸促进在无溶剂条件下，使用各种取代的硝基烯烃以中等至良好的收率进行。
• Iodine-catalyzed 1,4-addition of 2-(trimethylsilyloxy)furan to α,β-unsaturated ketones: a facile synthesis of γ-butenolides
  作者：J.S. Yadav、B.V. Subba Reddy、G. Narasimhulu、N. Sivasankar Reddy、P. Janardhan Reddy

  DOI：10.1016/j.tetlet.2009.02.128

  日期：2009.7

  The alpha,beta-unsaturated compounds undergo smooth conjugate addition with 2-(trimethylsilyloxy)furan (TMSF) in the presence of 10 mol % of iodine under mild and neutral conditions to afford the corresponding gamma-substituted butenolides in high yields and with good diastereoselectivity. The use of iodine makes this procedure simple, convenient and cost effective. (C) 2009 Published by Elsevier Ltd.
• Direct Asymmetric Michael Addition to Nitroalkenes: Vinylogous Nucleophilicity under Dinuclear Zinc Catalysis
  作者：Barry M. Trost、Julien Hitce

  DOI：10.1021/ja809723u

  日期：2009.4.8

  Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the gamma-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity.
• Inverting the Diastereoselectivity of the Mukaiyama–Michael Addition with Graphite-Based Catalysts
  作者：Maria Rosaria Acocella、Marco Mauro、Laura Falivene、Luigi Cavallo、Gaetano Guerra

  DOI：10.1021/cs401053t

  日期：2014.2.7

  Here, we show that graphite-based catalysts, mainly graphite oxide (GO) and exfoliated GO, are effective recyclable catalysts for a relevant stereoselective Mukaiyama-Michael addition, outperforming currently available catalysts. Moreover, the graphite-based catalysts described here invert the diastereoselectivity relative to that observed with known catalysts, with the unprecedented large prevalence of the anti diastereoisomer. This inverted diastereoselectivity is increased when the catalyst concentration is reduced and after catalyst recycling. Density functional theory calculations suggest that the selectivity is determined by two types of supramolecular interactions operating between the catalyst and the substrates at the diastereoselectivity-determining transition state, specifically, the pi-stacking of beta-nitrostyrene with graphite and the van der Waals interaction between the SiMe3 group of the silyl ether and the graphite.